Methyl iodide → Methyl 6-bromo-3-methoxypyridine-2-carboxylate

HRID 2201524Notes

Reaction equation

HRID 2201524 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[C:5]([OH:12])=[CH:4][CH:3]=1.CI.[C:15]([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[C:5]([O:12][CH3:15])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 22175135Methyl 6-bromo-3-hydroxypicolinate

Product 1

HCID 70700803Methyl 6-bromo-3-methoxypyridine-2-carboxylateYield 42.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl 6-bromo-3-hydroxypicolinate (10.0 g, 43.10 mmol), MeI (12.3 g, 86.66 mmol) and K2CO3 (12.0 g, 86.83 mmol) in DMF (100 mL) was stirred at RT overnight. Then the reaction mixture was concentrated, diluted with water and extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated to give methyl 6-bromo-3-methoxypicolinate (4.5 g, yield 42%). 1H-NMR (CDCl3, 400 MHz) δ 7.55 (d, J=8.8 Hz, 1H), 7.24 (d, J=8.8 Hz, 1H), 3.94 (s, 3H), 3.90 (s, 3H). MS (M+H)+: 246/248.

Workup

  1. concentrationThen the reaction mixture was concentrated
  2. additiondiluted with water
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a4171e8253404c1ea9a7c66a2bfccc15
Source dataset
uspto-grants-2016_06
Patent number
US09364482B2

Reaction notes

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